The present invention relates to phenolic compounds and polymers derived therefrom. The invention also relates to methods for making phenolic compounds and polymers derived therefrom.
Phenolic compounds are used in the synthesis of a wide variety of chemical products, particularly in the production of plastics and other bulk specialty products. Phenolic compounds bearing at least two reactive functional groups, at least one of which is a phenolic moiety, are commonly used to prepare polymers, particularly condensation polymers. One example is the polymerization of bis(phenols) with phosgene to prepare polycarbonates. In some cases mixtures of monomers, each bearing at least two nucleophilic groups, are used in a polymerization process with a separate monomer bearing two electrophilic groups to tailor properties of the resulting polymer. An example is the preparation of a polyestercarbonate through reaction of phosgene with a mixture of a "hard-block" monomer such as bisphenol-A and a "soft-block" monomer such as an aliphatic alpha-omega dicarboxylic acid, for example dodecanedioic acid. Such polyestercarbonates (for example, LEXAN of General Electric Plastics) typically retain the high impact strength which is the hallmark of polycarbonate resin while offering superior melt and flow characteristics relative to the corresponding polycarbonate made without soft-block monomer.
Soft-block monomers such as aliphatic alpha-omega dicarboxylic acids are typically produced by conversion processes based upon the use of non-renewable petrochemical feedstock. These multi-step chemical conversion processes typically produce unwanted hazardous byproducts which result in yield losses and must be destroyed before they are released to the environment. Disposal of a hazardous waste stream greatly adds to the cost of production. In addition, the organic chemical synthesis of long-chain diacids is limited by the starting materials used, and each chemical synthesis process can produce only one species of diacid. Soft-block monomers such as aliphatic alpha-omega dicarboxylic acids may also be prepared by biological fermentation as described in U.S. Pat. No. 6,066,480. However, fermentation processes often have less than optimum productivity and space-volume rates for economic production.
New types of phenolic compounds which may serve, for example, as monomers in condensation polymerization processes are constantly being sought. In particular, new types of phenolic compounds are needed which bear at least two functional groups, at least one of which is a phenolic moiety, which can serve as soft-block monomers in condensation polymerization. Also, new methods for the production of phenolic compounds are needed which have economic advantage over more commonly known methods such as synthesis from smaller hydrocarbon fragments.